The 10 Christmas Songs That Reduce Me To Actual Tears Every Single Freaking Year

Do you hear that? That’s the sound of me sobbing through a mouthful of gingerbread cookies.
Publish date:
December 25, 2014
music, christmas songs

I swear I’m not a big crier.

But catch me around Christmas and you would think that I’m an emotional train wreck. There’s just something about the music that turns me into a big sobbing mess of a human being.

I’m not talking about the goofy sing-a-long tunes (you know the offenders: “All I Want For Christmas Is My Two Front Teeth” and “Grandma Got Run Over By a Reindeer”). No. Fuck that noise.

I’m talking about the songs that make me go from this to this by the final verse. Why? Well, it’s complicated. Christmas is complicated. Christmas, the “happiest time of the year” is -- at the same time -- the saddest time of the year.

I’m not trying to put a damper on your twinkly-lights-and-sugar-coated-cookie holiday cheer. Far from it. The holidays remind me of happy memories, but it also reminds me of the ones I’d rather forget and the ones that harken to a time in my life to which I can no longer return. Taking a moment (or three minutes), to immerse myself into a song that transports me back to a time when everything seemed merry and bright, reminds me that things are still merry and bright.

Here are the songs that fill me up with bittersweet joy and bring me to tears, including Faith Hill. (Damn you, Faith. You do this to me every year.)

“Where Are You Christmas?” by Faith Hill

Somewhere along the way, we fall out of touch with Christmas. It goes from believing in Santa, stuffing your face with mom’s cookies, and unwrapping presents…to standing in the Post Office all day, failing miserably at that Pinterest recipe, and patiently listening to Great Aunt Tammy who won’t shut up about a 20-year-old argument she has with your mother. (The magic probably got lost somewhere at the post office.)

But then there are quiet moments -- eggnog in hand, looking up at the lights -- when I remember what it was like to be a kid waking up on Christmas morning. And this song reminds me of the emotional rollercoaster that is loving, losing, and rediscovering the magic of Christmas.

“One Little Christmas Tree” by Stevie Wonder

If you didn’t think Christmas trees have feelings, think again. There’s nothing like personifying a dejected, homeless Christmas tree to make you cry. (We are all that one little Christmas tree, aren’t we guys?) God forbid this song play in the parking lot while I’m picking my tree out -- this makes me want to take ALL of the Christmas trees home with me.

“Have Yourself a Merry Little Christmas” by Bright Eyes

There have been dozens of different renditions by dozens of artists over the years. Just take your pick: Judy Garland, Frank Sinatra, She & Him, Ella Fitzgerald, Luther Vandross, the Jackson 5, (even Relient K, if you want a fist-bumper). But for some reason, the one that gets me every time is the cover done by Bright Eyes. There’s a haunting quality to it -- just the tinkling of a piano, the emotional moan of a violin, and the soft vocals. And then read up on the history to those lyrics and the song takes a whole new meaning. Seriously. Waterworks.

“Christmas Shoes” by NewSong

I know, I know. Worst holiday song ever, right? Do I even need to explain this one? A little boy wants to buy a pair of shoes for his dying mother. As much as I want to hate this one like everyone else, I can’t do it.

Let me explain: I was seven years old when my Nana was dying of breast cancer. She always believed that elephants with upturned trunks were good luck. I saved up my quarters and bought an elephant charm bracelet at a flea market, and gave it to her, holding a small, naive hope in my heart that the elephant bracelet would save my Nana. It didn’t. But it didn’t stop me from believing that I could make her last moments on earth glimmer with hope.

“Fairytale of New York” by The Pogues

Maybe this is just a New York thing, but this song reminds me of walking through the streets on a gray winter day. You know, the cheerless days when it’s almost Christmas without a snowflake in sight. The duet between Shane MacGowan and Kirsty MacColl, sang in an Irish folk-style, is an invigorating twist on the typical background noise of jingle bells, laughing kids, and heavenly choir. Despite the ballad’s title, there’s no posturing. It’s gritty and real and down to earth. And this line gets me every time: “I’ve built my dreams around you.”

“Angels We Have Heard On High” by Christina Aguilera

You know that glorious moment after a snowstorm when the clouds break and the blue skies open up and the sun shines brilliantly on the mounds of new-fallen snow? If you interpreted that into a song, this cover by Christina Aguilera featuring Eric Dawkins would be it. I’ve owned Christina’s Christmas album since it first came out back in the day and I haven’t stopped listening to it. You can’t help but jump to your feet and clap along to this one. And when the crescendo kicks in? Chills.

“Christmas Lights” by Coldplay

Even if you have an “Ew, it’s Coldplay” mentality, this will free your Grinch heart. We have a tradition in my family of driving through the neighborhood to look at the lights, oohing and ahhing over the rows of houses, strung up from top to bottom. There’s a childlike wonder that I’ve never lost looking at those twinkling white lights. And my dad -- who taught me all about “exterior illumination” -- always loved them too. I know that when he’s gone, I’ll see my father in those lights.

“Grown-up Christmas List” by Kelly Clarkson

A few years ago, I stopped knowing what I “wanted” for Christmas. Every year since I was little, my mom would prod me starting in the fall “What do you want for Christmas?” And when I was little, they were stupid kid things: CDs, Beanie Babies, the latest Harry Potter book. But I grew up and stopped having an answer for her. I simply reply, “Anything you’d think I would love.”

I didn’t care about presents or cards or packages. Sure, I was grateful for little tokens of love. But more importantly, I’m genuinely grateful for another Christmas with my parents, friends, and all in happy health. (Oh, and that I could pay my rent this month. Always grateful for that.)

“So This Is Christmas” by John Lennon

It starts simply with John Lennon asking me, “So this is Christmas and what have you done?” Besides reminding me of all the stuff I haven’t done (just kidding), it does cause me to pause and reflect on my year. Sometimes, the year looked good. Others, it didn’t. But I can always pinpoint a few moments in my mind when I was smiling or belly-laughing or realizing something new so by Christmas, I can’t say that the year was all around awful.

“Better Days” by the Goo Goo Dolls

The holidays are over, the year is coming to a close, and all that’s left to consider is the new year facing us. Ever since “Iris,” it was love at first listen for me and the Goo Goo Dolls. Even though this is really more of a New Year’s Eve jam, the orchestral sweep paired with the crying out of vocals just send me over the edge every time. Even if I’ve had massive screw-ups in the year prior, it reassures me that “better days” are ahead of me. After all, “Tonight’s the night the world begins again.”

Which holiday songs make you cry? Which songs renew your hope for a happier year? Which songs bring you back to childhood? Share them with me! (And then, we can cry into our gingerbread cookies together.)